The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

SENGUL M. E., GULTEKIN D., Essiz S., ŞAHİN E., DAŞTAN A.

TETRAHEDRON, cilt.65, sa.25, ss.4859-4865, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 65 Sayı: 25
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1016/j.tet.2009.04.034
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4859-4865
  • Anahtar Kelimeler: Benzobarrelene, Bromination, Benzosemibullvalene, Polybromides, Polychlorides, Polyhalogenides, HIGH-TEMPERATURE BROMINATION, PI-METHANE REARRANGEMENT, 2,3-DIBROMOBENZOBARRELENE, PHOTOCHEMISTRY, BARRELENE, BENZONORBORNADIENE, INTERCONVERSIONS, PHOTOOXYGENATION, ISOMERIZATION, SUBSTITUENTS
  • Atatürk Üniversitesi Adresli: Evet

Özet

New polyhalogenated benzobarrelenes were synthesized in good yields. The bromination reaction of benzobarrelenes at high temperature gives non-rearranged products. Dehydrobromination of the formed products with t-BuOK yielded the desired polyhalogenated benzobarrelenes. The elimination reaction of cyclopropanoid dibromide with a base unusually resulted in the formation of a benzosemibullvalene derivative. (C) 2009 Elsevier Ltd. All rights reserved.